.closest()only looking for ancestor elements for initial selection. You need a combination of .closest()and .siblings()or .children():
//find closest parent `<li>` element and then find that element child `<label>` element
$('#start').closest('li').children('label');
//find the closest parent `<div>` element and then find that element sibling `<label>` element
$('#start').closest('div').siblings('label');
Update
A very fast selector will use .prev()twice and .parent()as follows:
$('#start').parent().prev().prev();
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